NP-MRD: Showing NP-Card for Metasequoic acid A (NP0140463)

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Record Information

Version

2.0

Created at

2022-06-29 21:35:40 UTC

Updated at

2022-06-29 21:35:40 UTC

NP-MRD ID

NP0140463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metasequoic acid A

Description

Metasequoic acid A, also known as metasequoate a, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Metasequoic acid A was first documented in 2016 (PMID: 27245322). Based on a literature review very few articles have been published on Metasequoic acid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    0.1255    2.5016   -1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0602    1.2242   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5072    0.2420   -2.1734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5416   -0.6943   -1.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0923   -0.0235   -0.3274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4186   -0.5272    0.0712 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3616   -0.7986   -1.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7960   -1.0168    1.3846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9690    0.4339    1.1319 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9099    1.3528    1.6497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071    0.6538    1.9623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394   -0.0647    0.7494 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7429   -1.4819    1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    0.6718    0.2399 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4169   -0.1403    0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5415    0.8194   -0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8470    0.0647   -0.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829   -0.6032    0.9276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5336   -0.0181   -1.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7908   -0.7125   -1.5752 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3867   -0.7452   -2.6817 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3941   -1.3744   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0423    2.8714   -2.4120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4473    3.1719   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3493   -0.3116   -2.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9728    0.8567   -2.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -1.6919   -1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3440   -0.8080   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014    1.0655   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301    0.0519   -1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3994   -0.8896   -0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1382   -1.7693   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7703   -1.5873    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258   -1.2902    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9417    0.8927    0.9645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7378    2.2347    0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742    1.7789    2.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995    0.0135    2.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921    1.4766    2.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -2.1833    0.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -1.8461    0.8408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474   -1.5965    2.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3748    1.5533    0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4198   -0.9396   -0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7240   -0.4954    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.6087    0.5393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328    1.2545   -1.2200 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3837   -0.1719    1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804   -0.4981    1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5256   -1.6945    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1233    0.4779   -2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3751   -1.2981   -0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 17 19  2  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 12 14  1  0
 12  5  1  0
  9  6  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 16 46  1  0
 16 47  1  0
 15 44  1  0
 15 45  1  0
 14 43  1  1
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  7 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 13 40  1  0
 13 41  1  0
 13 42  1  0
 19 51  1  0
 22 52  1  0
M  END


  Mrv1652306292223352D          

 22 24  0  0  1  0            999 V2000
    6.3659   -2.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5463   -1.9533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0546   -2.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824   -3.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8907   -4.0353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2020   -3.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2185   -1.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3989   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711   -0.3446    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5629    0.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3824    0.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350    1.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4155    1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9237    0.5071    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2516   -0.2499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7598   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9403   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -0.0607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1042    0.6018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2846    0.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988    1.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5794   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 20  1  6  0  0  0
 19 21  1  1  0  0  0
 15 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0140463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC[C@H]1C(=C)CC[C@H]2[C@@]3(C)C[C@H]3CC[C@]12C)=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13(11-18(21)22)5-7-16-14(2)6-8-17-19(16,3)10-9-15-12-20(15,17)4/h11,15-17H,2,5-10,12H2,1,3-4H3,(H,21,22)/b13-11+/t15-,16+,17-,19-,20+/m1/s1

> <INCHI_KEY>
PCLDEDSUWNZZDJ-BDBJVFIPSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.107986394440104

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-[(1aR,3aR,4S,7aS,7bS)-3a,7b-dimethyl-5-methylidene-decahydro-1H-cyclopropa[a]naphthalen-4-yl]-3-methylpent-2-enoic acid

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.858309513

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.816420390366828

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.0666

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(1aR,3aR,4S,7aS,7bS)-3a,7b-dimethyl-5-methylidene-octahydrocyclopropa[a]naphthalen-4-yl]-3-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      11.883  -3.823   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.353  -3.646   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.435  -4.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.047  -6.296   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.129  -7.533   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      11.577  -6.473   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.741  -2.233   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.211  -2.056   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.599  -0.643   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.517   0.593   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.047   0.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.905   2.007   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.376   2.183   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.458   0.947   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.070  -0.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.152  -1.703   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.622  -1.526   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.010  -0.113   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.928   1.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.398   1.300   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.104   2.653   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.682  -1.880   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14    9   16   22                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   14   20   21                                             
CONECT   20   19   18                                                       
CONECT   21   19                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Metasequoate a	Generator

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C(CC[C@H]1C(=C)CC[C@H]2[C@@]3(C)C[C@H]3CC[C@]12C)=C/C(O)=O

InChI Identifier

InChI=1S/C20H30O2/c1-13(11-18(21)22)5-7-16-14(2)6-8-17-19(16,3)10-9-15-12-20(15,17)4/h11,15-17H,2,5-10,12H2,1,3-4H3,(H,21,22)/b13-11+/t15-,16+,17-,19-,20+/m1/s1

InChI Key

PCLDEDSUWNZZDJ-BDBJVFIPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Unsaturated fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

33823893

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124708147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kushwaha V, Saxena K, Verma R, Verma SK, Katoch D, Kumar N, Lal B, Murthy PK, Singh B: Antifilarial activity of diterpenoids from Taxodium distichum. Parasit Vectors. 2016 May 31;9(1):312. doi: 10.1186/s13071-016-1592-4. [PubMed:27245322 ]

Showing NP-Card for Metasequoic acid A (NP0140463)

MOL for NP0140463 (Metasequoic acid A)

3D MOL for NP0140463 (Metasequoic acid A)

3D SDF for NP0140463 (Metasequoic acid A)

3D-SDF for NP0140463 (Metasequoic acid A)

PDB for NP0140463 (Metasequoic acid A)

3D PDB for NP0140463 (Metasequoic acid A)

SMILES for NP0140463 (Metasequoic acid A)

INCHI for NP0140463 (Metasequoic acid A)

Structure for NP0140463 (Metasequoic acid A)

3D Structure for NP0140463 (Metasequoic acid A)